Madonna has been a style icon for almost four decades, but the Nineties marked an interesting period of transformation for the pop legend. She kicked off the era in a notorious cone-shaped bra designed by Jean Paul Gaultier and ended it in a heroic red kimono created by the same man. That's a lot of style terrain to cover, but it harmonized intelligently with the evolution of Madonna's musical and lyrical themes. While her Blonde Ambition Tour celebrated sexual exploration and liberation, the singer became more concerned with other forms of identity and social politics by the decade's midpoint. In 1995's "Bedtime Story," Madonna took a sharp turn into the left field, pairing ambient pop production with Mark Romanek's surrealist direction for its video, which remains one of her best. She appeared as an empress from another dimension in the clip, which carried heavy spiritual connotations.
By decade's end, Madonna was a Kabbalah devotee and self-aware 40-year-old who still knew how to set fire to the dance floor. Her Asian-inspired, slightly gothic wardrobe of 1998 and 1999 still represents a unique chapter in the style story of any pop star.